Azodyestuff



Patented Jan. 29, 1935 UNITED S ATE AZODYEST'UFF Heinrich Clingestein,Cologne-on tlie-Bhine; Myrtil Kahn, Cologne-Ricki, Germany, assignors toGeneral Aniline Works, Inc., New ,York,

N. Y., a corporation of Delaware No Drawing. Application June 29, 1 933,Serial No. 678,312. In Germany July 26, 1932 4 Claims.

The present invention relates to new azodye stufis. More particularly itrelates to dyestuffs which may be represented by the probable generalwherein one :0 stands for a sulfonic acid group,

the other :1: stands for hydrogen, and R stands for the radical of am-arylenediamine being at least once substituted in one amino group by ahydroxyalkyl group, for example B may stand for the radical ofm-phenylenediamine which is substituted in one amino group byhydroxymethyl, hydroxyethyl, hydroxypropyl, a glycol radical, aglycerine radical and the like, or for a m-phenylenediamine containingin each amino group one of the afore-mentioned substituents, or in whichthe two hydrogen atoms of one amino group are substituted by thesesubstituents.

Our new dyestuffs can be prepared by monodiazotizing thediaminodisazodyestuff, obtainable by saponifying or reducingrespectively the monoazodyestufi from diazotized l-amino-l-acetylaminoor-4-nitrobenzene respectively and laminonaphthalene-G- or -7-sulfonicacid, monodiazotizing and coupling with2-amino-8-hydroxynaphthalene-G-sulforfic' acid in alkaline solution,mono-diazotizing and coupling with a m-arylenediamine being at leastonce substituted in one amino group by a hydroxyalkyl group.

Our new dyestuffs are in form of their alkali metal salts generally darkpowders, soluble in water, dyeing cotton generally full black shades ofgood fastness properties.

The invention is illustrated by,the following example, without beinglimited thereto:

ExampZe.-32.4 parts by weight of the aminoazodyestufi prepared bysaponifying the dyestuff from diazotized l-amino-4-acetylaminobenzene vand l-aminonaphthalene-S- (-7) sulfonic acid or by reducing thecorresponding azodyestuff prepared by means of 1-amino-4-nitrobenzene asdiazotization component are diazotized in the usual manner with 6.9parts by weight of sodium nitrite and hydrochloric acid and coupled with23.9 parts by weight of 2-amino-8-hydroxynaphthalene-fi-sulfonic acid inalkaline solution. The dyestuff formed is salted out, pressed, pastedwith water and ice, then 25 parts by weight of sulfuric acid of 40 B.are added, and diazotization is performed by the addition of 6.9 partsby (Cl. 260-72)v weight of sodium nitrite; The diazotization mixture isthen added to a soda-alkaline solution of 16 parts by'weight of1-hydroxyethylamino-3-' aminobenz'ene When the coupling is complete,some salt is a'ddedjjandthe mass is filtered, 1 pressed'and"dried.""'I'he dyestuff contains the free amino group in thenaphthalene nucleus which bears no hydroxy group. In its free state thedyestuff corresponds to the following probable formula? HOaS N j 0H iSOaH -N= QNH-bm-om-oH NHa We claim:

1. Azodyestuffs having in the free state the following formula:

H0315 III I OH a N=N-R wherein one :1: stands for a sulfonic acid group,the other 3: stands for hydrogen, and R stands for the radical of am-phenylenedi-amine being at least once substituted in one amino groupby a hydroxyalkyl group, being in form of their alkali metalsaltsgenerally dark powders, soluble in water, dyeing cotton generally fullblack shades of good fastness properties.

in Water, dyeing, cotton generally full. black shades of good fastnessproperties.

4. The azodyestufi having in the free state the 3. Azodyestufis havingin the free state the formula: following formula: a 5

egg a. m H033 1 l I l OH OH S03 10 N=N NH-OHz-CHrOH N=NR being inform'of its alkali metal saltsa dark powder, dyeing cotton fullbla'ck'shadesof'good fastness properties.

HEINRICH CLINGESTEIN. MYRTI L KAHN.

whereinone :1: stands fora sulfonic acid group, 15 the other :1: standsf c'arfhydrogen, and R stands for the 'radical ofa' mephenylenediaminebeing at least once substituted in oneiamino group by a hydroxyethylgroup, being in formof their alkali metal salts generally; dark powders,"soluble

